Hydrochloric Acid → N-[5-[4-(5-{[(2R,6S)-2,6-Dimethyl-4-morpholinyl]methyl}-1,3,4-oxadiazol-2-yl)-1H-indazol-6-yl]-2-(methyloxy)-3-pyridinyl]-2-(methyloxy)benzenesulfonamide

HRID 38891

Reaktionsgleichung

Reaktionsgleichung von HRID 38891
[CH3:1][C@H:2]1[O:7][C@@H:6]([CH3:8])[CH2:5][N:4]([CH2:9][C:10]2[O:14][C:13]([C:15]3[CH:23]=[C:22]([C:24]4[CH:25]=[C:26]([NH2:32])[C:27]([O:30][CH3:31])=[N:28][CH:29]=4)[CH:21]=[C:20]4[C:16]=3[CH:17]=[N:18][N:19]4S(C3C=CC(C)=CC=3)(=O)=O)=[N:12][N:11]=2)[CH2:3]1.[CH3:43][O:44][C:45]1[CH:50]=[CH:49][CH:48]=[CH:47][C:46]=1[S:51](Cl)(=[O:53])=[O:52].N1C=CC=CC=1.[OH-].[Na+].Cl>C(Cl)(Cl)Cl.O1CCOCC1>[CH3:8][C@H:6]1[O:7][C@@H:2]([CH3:1])[CH2:3][N:4]([CH2:9][C:10]2[O:14][C:13]([C:15]3[CH:23]=[C:22]([C:24]4[CH:25]=[C:26]([NH:32][S:51]([C:46]5[CH:47]=[CH:48][CH:49]=[CH:50][C:45]=5[O:44][CH3:43])(=[O:53])=[O:52])[C:27]([O:30][CH3:31])=[N:28][CH:29]=4)[CH:21]=[C:20]4[C:16]=3[CH:17]=[N:18][NH:19]4)=[N:12][N:11]=2)[CH2:5]1

Komponenten

8

Edukt 5

HCID 313Hydrochloric AcidHCID 1049PyridineHCID 14798Sodium HydroxideHCID 37458512-Methoxybenzenesulfonyl ChlorideHCID 666936135-{4-(5-{[(2R,6S)-2,6-Dimethyl-4-morpholinyl]methyl}-1,3,4-oxadiazol-2-yl)-1-[(4-methyl phenyl)sulfonyl]-1H-indazol-6-yl}-2-(methyloxy)-3-pyridinamine

Produkt 1

HCID 66691331N-[5-[4-(5-{[(2R,6S)-2,6-Dimethyl-4-morpholinyl]methyl}-1,3,4-oxadiazol-2-yl)-1H-indazol-6-yl]-2-(methyloxy)-3-pyridinyl]-2-(methyloxy)benzenesulfonamideAusbeute 39 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 6212ChloroformLösungsmittelHCID 312751,4-DioxaneLösungsmittel

Versuchsvorschrift

5-{4-(5-{[(2R,6S)-2,6-Dimethyl-4-morpholinyl]methyl}-1,3,4-oxadiazol-2-yl)-1-[(4-methylphenyl)sulfonyl]-1H-indazol-6-yl}-2-(methyloxy)-3-pyridinamine (150 mg, 0.254 mmol) was dissolved in chloroform (3 ml) then 2-(methyloxy)benzenesulfonyl chloride (79 mg, 0.382 mmol) was added. Pyridine (0.082 ml, 1.018 mmol) was added to the reaction mixture and it was stirred at room temperature for 5 h. The compound was dissolved in 1,4-dioxane (2 ml) and 2M sodium hydroxide (2 ml) and stirred at room temperature for 3 h. The reaction mixture was neutralized to pH 7 with 2M HCl, then the solvent was removed under a stream of nitrogen. The solid was dissolved in DMSO then filtered through a filter tube and purified by Mass Directed Automated Preparative HPLC. The solvent was removed under nitrogen to give the title compound as a white solid (60 mg).

Aufarbeitung

  1. customthe solvent was removed under a stream of nitrogen
  2. dissolutionThe solid was dissolved in DMSO
  3. filtrationthen filtered through a filter tube
  4. custompurified by Mass Directed Automated Preparative HPLC
  5. customThe solvent was removed under nitrogen

Quellen und Nachweise

ORD-Eintrag
ord-806177adaf7443e9a48a684cd7ac6adb
Quelldatensatz
uspto-grants-2013_09
Patentnummer
US08524751B2

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